Thionyl Chloride → HCID 21852109, compound

HRID 617206Notes

Reaction equation

HRID 617206 reaction equation
[C:1]([CH:3]([C:5]1[CH:6]=[CH:7][C:8]([O:15][CH3:16])=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11])O)#[N:2].S(Cl)([Cl:19])=O>C(Cl)(Cl)Cl.CN(C=O)C>[Cl:19][CH:3]([C:5]1[CH:6]=[CH:7][C:8]([O:15][CH3:16])=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11])[C:1]#[N:2]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 19261483HCID 19261483, compound

Product 1

HCID 21852109HCID 21852109, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent

Procedure

To a suspension of methyl 5-(1-cyano-1-hydroxymethyl)-2-methoxybenzoate (2.15 g) in chloroform (40 ml) were added thionyl chloride (2.0 ml) and DMF (2 drops), and the mixture was refluxed for 30 minutes under heat. After cooling, the reaction mixture was washed with water, aqueous solution of sodium hydrogencarbonate and saturated brine in sequence and dried over anhydrous sodium sulfate. This was concentrated under reduced pressure to obtain 2.37 g of aimed compound as an oily product.

Workup

  1. temperaturethe mixture was refluxed for 30 minutes
  2. temperatureunder heat
  3. temperatureAfter cooling
  4. washthe reaction mixture was washed with water, aqueous solution of sodium hydrogencarbonate and saturated brine in sequence
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThis was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7043a2cda8694a2baecb0d3db84905e3
Source dataset
uspto-grants-1999_09
Patent number
US05948803

Reaction notes

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